Potassium Carbonate → HCID 23319117, compound

HRID 1981563Notes

Reaction equation

HRID 1981563 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].[Cl:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]OS(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 392115-Hydroxy-2-nitrobenzaldehydeHCID 561724HCID 561724, compound

Product 1

HCID 23319117HCID 23319117, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 16.7 g (100 mmol) of 5-hydroxy-2-nitrobenzaldehyde, 32 g (110 mmol) of 6-chlorohexyl-p-toluenesulfonate and 17 g of potassium carbonate in dry 250 ml of DMF was heated to 100° C. under dry nitrogen for 3 h. The reaction was cooled, filtered and evaporated to a dark oil. The crude product was dissolved in 500 ml of ethyl acetate, and the organic layer was washed twice with 300 ml of saturated sodium carbonate, and twice with 300 ml of brine, dried, filtered and evaporated. Filtration through silica gel gave 25.5 g (89.2 mmol, 89%) of 5-(6-chlorohexyl)oxy-2-nitrobenzaldehyde as a green syrup unstable to distillation.

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. customevaporated to a dark oil
  4. dissolutionThe crude product was dissolved in 500 ml of ethyl acetate
  5. washthe organic layer was washed twice with 300 ml of saturated sodium carbonate
  6. dry with materialtwice with 300 ml of brine, dried
  7. filtrationfiltered
  8. customevaporated
  9. filtrationFiltration through silica gel

Sources & evidence

ORD record
ord-50e1013b0deb4f5b801367dc498596d6
Source dataset
uspto-grants-1986_06
Patent number
US04593029

Reaction notes

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